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Synthesis and structure-activity relationships of new chiral spiro-β-lactams highly active against HIV-1 and Plasmodium

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dc.contributor.authorAlves, Nuno Guerreiro
dc.contributor.authorBártolo, Inês
dc.contributor.authorAlves, Américo J.S.
dc.contributor.authorFontinha, Diana
dc.contributor.authorFrancisco, Denise
dc.contributor.authorLopes, Susana M.M.
dc.contributor.authorSoares, Maria I.L.
dc.contributor.authorSimões, Carlos J.V.
dc.contributor.authorPrudêncio, Miguel
dc.contributor.authorTaveira, Nuno
dc.contributor.authorMelo, Teresa Pinho e
dc.date.accessioned2021-09-08T14:38:33Z
dc.date.available2021-09-08T14:38:33Z
dc.date.issued2021
dc.description© 2021 Elsevier Masson SAS. All rights reserved.pt_PT
dc.description.abstractThe synthesis and antimicrobial activity of new spiro-β-lactams is reported. The design of the new molecules was based on the structural modulation of two previously identified lead spiro-penicillanates with dual activity against HIV and Plasmodium. The spiro-β-lactams synthesized were assayed for their in vitro activity against HIV-1, providing relevant structure-activity relationship information. Among the tested compounds, two spirocyclopentenyl-β-lactams were identified as having remarkable nanomolar activity against HIV-1. Additionally, the same molecules showed promising antiplasmodial activity, inhibiting both the hepatic and blood stages of Plasmodium infection.pt_PT
dc.description.sponsorshipThe authors thank Coimbra Chemistry Centre (CQC), supported by the Portuguese Agency for Scientific Research, “Fundação para a Ciência e a Tecnologia” (FCT) through project UIDB/00313/2020 and UIDP/00313/2020, co-funded by COMPETE2020-UE. iMed. ULisboa, Faculdade de Farmácia de Lisboa, Portugal, is supported by FCT through Projects UIDB/04138/2020 and UIDP/04138/2020, co-funded by COMPETE2020-UE. Miguel Prudêncio acknowledges FCT for grant PTDC/SAU-INF/29550/2017. Nuno Guerreiro Alves and Américo J. S. Alves thank FCT for fellowships PD/BD/135287/2017 and SFRH/BD/128910/2017, respectively.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationEur J Med Chem. 2021 Jul 5;219:113439pt_PT
dc.identifier.doi10.1016/j.ejmech.2021.113439pt_PT
dc.identifier.eissn1768-3254
dc.identifier.issn0223-5234
dc.identifier.urihttp://hdl.handle.net/10451/49470
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.relation.publisherversionhttps://www.sciencedirect.com/journal/european-journal-of-medicinal-chemistrypt_PT
dc.subject3-Dipolar cycloadditionpt_PT
dc.subject2-Butynoatespt_PT
dc.subjectAllenespt_PT
dc.subjectAnti-HIV agentspt_PT
dc.subjectAntiplasmodial agentspt_PT
dc.subjectPhosphane-catalyzed [3+2] annulationspt_PT
dc.subjectSpiro-3H-pyrazole-β-lactamspt_PT
dc.subjectSpiro-penicillanatespt_PT
dc.subjectSpirocyclic compoundspt_PT
dc.subjectSpirocyclopentenyl-β-lactamspt_PT
dc.subjectβ-Lactamspt_PT
dc.titleSynthesis and structure-activity relationships of new chiral spiro-β-lactams highly active against HIV-1 and Plasmodiumpt_PT
dc.typejournal article
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oaire.citation.titleEuropean Journal of Medicinal Chemistrypt_PT
oaire.citation.volume219pt_PT
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person.givenNameInês
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person.givenNameDenise
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